Hydrochloric Acid → HCID 18314487, 화합물

HRID 277383노트

반응식

HRID 277383 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH:18]=1.CN(C)[C:21]1[O:22][C:23](=[O:31])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:26]=1.[C:33](=O)([O-])[O-].[K+].[K+].IC.Cl>C(O)(=O)C.CN(C)C=O.C(Cl)Cl.C(OCC)(=O)C>[CH3:33][N:26]1[C:25]([C:27]([F:30])([F:29])[F:28])=[CH:24][C:23](=[O:31])[N:1]([C:2]2[CH:3]=[CH:4][C:5]3[S:9][N:8]=[C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=3[CH:18]=2)[C:21]1=[O:22]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 18314476HCID 18314476, 화합물

생성물 1

HCID 18314487HCID 18314487, 화합물

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of ethyl 5-amino-α,α-dimethyl-1,2-benzisothiazole-3-acetate (0.546 g, 2.06 mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (0.430 g, 2.06 mmol) in acetic acid is refluxed for 4.5 hours, concentrated in vacuo, and diluted with saturated sodium hydrogen carbonate solution. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a brown foam. A solution of the foam in N,N-dimethylformamide is treazed with potassium carbonate (0.312 g, 2.25 mmol), stirred for one hour, treated with iodomethane (0.420 mL, 6.70 mmol), stirred overnight at room temperature, and poured into an ice-water mixture containing 20 mL of concentrated hydrochloric acid. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed sequentially with 10% hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown oil. Column chromatography of the oil using silica gel and a 33% ethyl acetate in methylene chloride solution affords a pink foam which is recrystallized from ethanol to give the title product as pink crystals, mp 164-167° C.

후처리

  1. temperatureis refluxed for 4.5 hours
  2. concentrationconcentrated in vacuo
  3. additiondiluted with saturated sodium hydrogen carbonate solution
  4. extractionThe resultant aqueous mixture is extracted with methylene chloride
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a brown foam
  9. stirringstirred overnight at room temperature
  10. extractionThe resultant aqueous mixture is extracted with methylene chloride
  11. washThe combined organic extracts are washed sequentially with 10% hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated in vacuo
  14. customto obtain a brown oil
  15. customis recrystallized from ethanol

출처 및 근거

ORD 기록
ord-77a40499f3fe424cabab2098b425babf
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355796B1

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